Conan Awkwardly Hits on Kate Upton While Playing Video Games

Kate Upton joined Conan O'Brien for "Clueless Gamer," where she thought she was just going to play a videogame with her friend Conan and then realized that he wanted to be more than just friends.

Conan described Upton as a "friend, partner, some would say soulmate." He then sat her down at a romantic candlelit dinner that happened to be nearby his gaming console. When Antonio the violinist came out to serenade them it started to get awkward.

Conan tried a variety of ways to win Upton's affection including asking her if she noticed his cologne and suggesting that they play a game using one controller. "You can take your other hand and put it on top of my hand if you want to, " he said to her.

When they won the game with the four hand one controller approach Conan said, "When I suggested we work together, our bodies touching, it felt like we became one person." Kate said, "Yeah, I was able to help you experience winning."

In the end, Conan realized he and Kate weren't soul mates so he let her know there were no hard feelings by bringing out Antonio the violinist one more time.

In "Clueless Gamer," Conan reviews video games with celebrity guests. In this case he was checking out XBox's Cuphead which is available September 29th. The game was inspired by 1930's cartoons and features cooperative play.